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DMAP-Catalyzed Diastereoselective [3+2] Annulation of Isatin-Derived MBH Carbonates and 3-Methyleneoxindoles: Tempting Two Adjacent Quaternary Spirocenters

delete2026-06-28
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PRE
AI
R
Rohtash Kumar
A
Akanksha Santosh Deshpande
V
Vinod K. Singh *
DOI：10.1002/ajoc.70478delete
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Abstract

Abstract

En 中文
A highly diastereoselective synthesis of bis-spirooxindoles has been achieved via a [3+2] annulation reaction using MBH carbonates with 3-methyleneoxindoles. By utilizing DMAP (20 mol%) as an organocatalyst under mild reaction conditions, a versatile bis-spirooxindole has been synthesised in good to high yield (up to 93%) and excellent diastereoselectivities (up to >20:1). The robustness of this methodology is demonstrated through scale-up experiments and straightforward post-synthetic transformations. Moreover, based on the reaction result, a plausible reaction mechanism is proposed.
Keywords:
MBH carbonate
DMAP-catalyzed
[3+2] annulation
spirooxindole

Journal

Asian Journal of Organic Chemistry cover
Asian Journal of Organic Chemistry
IF:
2.7
Papers:
938
Citations:
6.5K

Organization

I
indian institute of technology
Scholars:
2.2K
Papers: 1.0K
Citations: 0
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